1-Ethyl (αS)-α-[[(1S)-1-carboxy-5-[(2,2,2-trifluoroacetyl)amino]pentyl]amino]benzenebutanoate

250 mL of a three-necked flask was added 20.8 g of ethyl (R) -2-hydroxy-4-phenylbutanoate, 110 mL of dichloromethane and 42.4 gSodium carbonate, slowly adding 26.6 g of p-toluenesulfonyl chloride at 0 ° C, raising the temperature of the liquid to 25 ° C for 8 hours; filtering the reaction solution, To the filtrate was added 62.3 g of trifluoroacetyl lysine tetramethylammonium salt at 15 ° C for 10 hours. The reaction mixture was filtered and the filtrate was distilled off under reduced pressure to give methylene chloride. The residue was added with 240 mL of n-hexane and stirred at 0 to 5 ° C for 5 hours to obtain 37.2 gN2- [1- (S) -ethoxycarbonyl-3-phenylpropyl] -N6-trifluoroacetyl-L-lysine, The yield was 86.0percent and the HPLC purity was 98.6percent.250 mL of a three-necked flask was added 20.8 g of (R)-2-hydroxy-4-phenylbutyric acid ethyl ester, 150 mL of tetrahydrofuran and 20.2 g of triethylamine were added slowly at 0 ° C to a solution of 12.6 g of methanesulfonyl chloride and the temperature was raised to 25 ° C for 8 hours. The reaction solution was filtered and 37.2 g lithium salt of trifluoroacetyl lysine And the reaction was stirred at 25 ° C for 10 hours.The reaction mixture was filtered and the filtrate was distilled under reduced pressure to remove tetrahydrofuran. The residue was added to 85 mL of ethanol and stirred at 0 ° C for 5 hours to obtain 35.9 g of N2- [1- (S) -ethoxycarbonyl-3-phenylpropyl] -N6- Trifluoroacetyl-L-lysine, yield 83.0percent, HPLC purity 98.9percent.(R) -2-hydroxy-4-phenylbutyric acid ethyl ester, 150 mL of tetrahydrofuran and 19.8 gPyridine, 13.5 g of methanesulfonyl chloride was slowly added at 0 ° C, and the temperature was raised to 35 ° C. The reaction was stirred for 6 hours. The reaction solution was filtered and 39.6 g of trifluoroacetyl lysine sodium salt was added to the filtrate, The reaction was stirred at 25 ° C for 10 hours.The reaction mixture was filtered and the filtrate was distilled under reduced pressure to remove tetrahydrofuran. The residue was added with 40 mL of cyclohexane and 200 mL of cyclohexane and stirred at 0 ° C for 8 hours to prepare 36.6 g of N2- [1- (S) -ethoxycarbonyl-3- Phenylpropyl] -N6-trifluoroacetyl-L-lysine, yield 84.7percent, HPLC purity 98.8percent.

Lisinopryl intermediate

Molecular Weight:432.4
XLogP3:1.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:14
Exact Mass:432.18720645
Monoisotopic Mass:432.18720645
Topological Polar Surface Area:105
Heavy Atom Count:30
Complexity:551
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes